Acetic acid (E)-2-((2R,3R,6S)-6-dimethoxymethyl-3-methyl-tetrahydro-pyran-2-yl)-3-{(1S,2S,3R)-2-[(S)-2-(4-methoxy-2-oxo-2,5-dihydro-furan-3-yl)-1-methyl-2-oxo-ethyl]-3-methyl-cyclohexyl}-allyl ester

Base Information

• Chemical Name: Acetic acid (E)-2-((2R,3R,6S)-6-dimethoxymethyl-3-methyl-tetrahydro-pyran-2-yl)-3-{(1S,2S,3R)-2-[(S)-2-(4-methoxy-2-oxo-2,5-dihydro-furan-3-yl)-1-methyl-2-oxo-ethyl]-3-methyl-cyclohexyl}-allyl ester
• CAS No.: 131507-82-9
• Molecular Formula: C₂₉H₄₄O₉
• Molecular Weight: 536.663

Synonyms:

Chemical Property of Acetic acid (E)-2-((2R,3R,6S)-6-dimethoxymethyl-3-methyl-tetrahydro-pyran-2-yl)-3-{(1S,2S,3R)-2-[(S)-2-(4-methoxy-2-oxo-2,5-dihydro-furan-3-yl)-1-methyl-2-oxo-ethyl]-3-methyl-cyclohexyl}-allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (E)-2-((2R,3R,6S)-6-dimethoxymethyl-3-methyl-tetrahydro-pyran-2-yl)-3-{(1S,2S,3R)-2-[(S)-2-(4-methoxy-2-oxo-2,5-dihydro-furan-3-yl)-1-methyl-2-oxo-ethyl]-3-methyl-cyclohexyl}-allyl ester

There total 1 articles about Acetic acid (E)-2-((2R,3R,6S)-6-dimethoxymethyl-3-methyl-tetrahydro-pyran-2-yl)-3-{(1S,2S,3R)-2-[(S)-2-(4-methoxy-2-oxo-2,5-dihydro-furan-3-yl)-1-methyl-2-oxo-ethyl]-3-methyl-cyclohexyl}-allyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methyl 30-O-acetyltetronasin (103576-53-0) + trimethyl orthoformate (149-73-5) → (2R,3S,5R)-2-((R)-2,2-Dimethoxy-1-methyl-ethyl)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan (131507-83-0) + Acetic acid (E)-2-((2R,3R,6S)-6-dimethoxymethyl-3-methyl-tetrahydro-pyran-2-yl)-3-{(1S,2S,3R)-2-[(S)-2-(4-methoxy-2-oxo-2,5-dihydro-furan-3-yl)-1-methyl-2-oxo-ethyl]-3-methyl-cyclohexyl}-allyl ester (131507-82-9)

Guidance literature:

With camphor-10-sulfonic acid; ozone; Yield given. Multistep reaction. Yields of byproduct given; 1.) dichloromethane, -78 deg C;

DOI:10.1016/S0040-4039(00)97889-4

Reference yield:

Acetic acid (E)-2-((2R,3R,6S)-6-dimethoxymethyl-3-methyl-tetrahydro-pyran-2-yl)-3-{(1S,2S,3R)-2-[(S)-2-(4-methoxy-2-oxo-2,5-dihydro-furan-3-yl)-1-methyl-2-oxo-ethyl]-3-methyl-cyclohexyl}-allyl ester (131507-82-9) → Benzoic acid (R)-2-benzenesulfonyl-1-{(2S,5R,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-acetyl]-5-methyl-tetrahydro-pyran-2-yl}-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-butyl ester

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / O₃ / CH₂Cl₂ / -29 °C

2: LiAlH₄ / tetrahydrofuran

3: imidazole / dimethylformamide

4: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

5: dimethylboron bromide / CH₂Cl₂ / -78 °C

6: 1.) t-BuLi / 1.) toluene, THF, -78 deg C 2.) -78 deg C

7: -78 °C

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; dimethylboron bromide; tert.-butyl lithium; ozone; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97889-4

Reference yield:

Acetic acid (E)-2-((2R,3R,6S)-6-dimethoxymethyl-3-methyl-tetrahydro-pyran-2-yl)-3-{(1S,2S,3R)-2-[(S)-2-(4-methoxy-2-oxo-2,5-dihydro-furan-3-yl)-1-methyl-2-oxo-ethyl]-3-methyl-cyclohexyl}-allyl ester (131507-82-9) → (2S,5R,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-acetyl]-5-methyl-tetrahydro-pyran-2-carbaldehyde (131507-85-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / O₃ / CH₂Cl₂ / -29 °C

2: LiAlH₄ / tetrahydrofuran

3: imidazole / dimethylformamide

4: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

5: dimethylboron bromide / CH₂Cl₂ / -78 °C

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; dimethylboron bromide; ozone; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97889-4

upstream raw materials:

methyl 30-O-acetyltetronasin

trimethyl orthoformate

Downstream raw materials:

(2S,5R,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-acetyl]-5-methyl-tetrahydro-pyran-2-carbaldehyde

2-(tert-Butyl-diphenyl-silanyloxy)-1-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-ethanone

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